For fans of the Washington Capitals, there have been much more than a handful of heartbreaking moments since the franchise opened up shop in 1974.
And perhaps more importantly, with the exception of the Washington Bullets' one national championship and the Redskins' trio of championships (the last of which coming in 1991), D.C. has had its fair share of disappointing performances from the city's professional sports teams.
What's made the Caps' recent struggles more frustrating has been that, at least on paper, Ted Leonsis' teams has been flush with star-caliber talents, but for whatever reason, Alex Ovechkin and company haven't been able to find their way beyond Round 2 of the Stanley Cup playoffs.
There's still more than a good chance that they'll get there soon, but for now, here's a look at the five most painful seasons in Capitals history.
During the 2009-10 regular season, the Capitals looked like the NHL's most dangerous team, as Bruce Boudreau's squad steamrolled through the Eastern Conference en route to the Presidents' Trophy, which is given to the team with the league's best record.
And in Round 1, the Caps faced the eighth-seeded Montreal Canadiens, who appeared to be heavily outclassed by a team that featured Ovechkin, Nicklas Backstrom, Alexander Semin and Mike Green at the height of their powers.
But Jaroslav Halak had other things in mind, and just as he'd done to Ovechkin at the Vancouver Olympics months before, the Slovakian stopper shut the Capitals down, and the Habs managed to upset the favorite in seven games.
What hurt even more for Capitals fans was that their heroes jumped out to a 3-1 series lead, but even with two opportunities to finish Montreal off on home ice, they just weren't able to solve Halak.
When Jaromir Jagr arrived in Washington in 2001, the Capitals appeared primed to take a compelling run at the franchise's first Stanley Cup, especially because the team was just three years removed from an Eastern Conference championship.
But even with Jagr, Robert Lang, Sergei Gonchar and fan favorites Peter Bondra and Olaf Kolzig, the Capitals were never able to put things together, and things came to a head during the 2003-04 season.
After watching his star-studded squad put forth mediocre efforts, Leonsis decided he'd seen enough and dealt Jagr, Lang (who was leading the league in points at the time), Gonchar, Bondra, Mike Grier and Anson Carter prior to the trade deadline.
Though it was a miserable season, it may have saved the franchise, as the team earned the right to select Alex Ovechkin with the No. 1 pick that summer.
During the 1980s, the Capitals appeared to be on the brink of something special.
They had a host of All-Stars in Rod Langway, Larry Murphy, Scott Stevens, Mike Gartner and Mike Ridley and looked like a team that could contend for the Cup.
And in Round 1 of the 1987 playoffs, the Caps stormed out of the gates to take a 3-1 series lead over the underdog New York Islanders, but as has been the case many times in team history, it wasn't enough.
The Isles fought back to tie the series, and during Game 7, Pat LaFontaine broke the hearts of Capitals fans by ending Washington's season with an opportunistic goal in the fourth overtime period.
As is the case with many expansion teams, the 1974-75 Washington Capitals struggled mightily during their first season in the National Hockey League.
In fact, this listless squad posted a dreadful 8-67-5 record, and the Capitals' paltry number of victories still stands as the NHL record for least wins by a team playing a schedule of at least 70 games.
Thankfully, the fan support wasn't overwhelming at this stage in the franchise's history, so not many were on hand to see arguably the worst NHL team in history compete.
The loan bright spot for this team may have been the emergence of the legendary (at least in D.C. circles) Yvon Labre, who went on to be the first player in franchise history to have his number retired by the Capitals.
Call me crazy, but I still hold the 2008-09 Capitals season as the most painful campaign in franchise history.
This team was coming off its second consecutive postseason berth, and with Ovechkin playing like the best player in the league, Backstrom looking like a top-flight playmaker, Green once again leading all rearguards in scoring and Semyon Varlamov seeming like the real deal, Washington figured to be a Stanley Cup contender.
And the Caps were for a time, as they clawed back from a 3-1 hole in Round 1 against the Rangers to force a Game 7 on home ice. Once they got there, former league MVP and three-time Stanley Cup winner Sergei Fedorov provided the dramatic flair, as the Russian legend authored a highlight-reel winning goal against New York with just moments remaining.
Unfortunately, the Caps faced their hated rivals from Pittsburgh in the next round. Sure, there were good times, such as when D.C. took a 2-0 series lead after Ovechkin and Sidney Crosby traded hat tricks in Game 2, but from there, it was just torture.
David Steckel's overtime goal in Game 6 helped Washington force a Game 7, but even with the clash taking place at the Verizon Center, the Caps were no match.
The game was essentially over before it really started, as Pittsburgh stormed out to a 4-0 lead before the second period was two minutes old. To make matters worse, the Pens would go on to win the Stanley Cup over Detroit, while Washington has never gotten closer since.